Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin

Abstract

Cu(II), Zn(II) and Re(I) complexes have been synthesized with the Schiff base, N'-[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H) which was prepared by condensation of S-benzyldithiocarbazate and 3-acetylcoumarin. The metal complexes were characterized on the basis of various physico-chemical and spectroscopic techniques including elemental analysis and electrochemical studies, and FT-IR, UV-Vis, NMR, EPR and mass spectroscopy. The Schiff base was found to behave as a bidentate ligand coordinating with Cu(II) and Zn(II) in the thiolate form with 1:2 metal to ligand stoichiometry. Crystals suitable for X-ray diffractometry (XRD) were obtained from the reaction of ReCl(CO)5 with SBCM-H forming a centrosymmetric dimeric complex Re2L2(CO)6 linked by Re-S-Re bridges, where S is the thiolate sulfur of the N,S-bidentate ligand. This Re(I) complex is the first metal carbonyl complex with a bidentate dithiocarbazate ligand to have been characterized by XRD. Cytotoxicity assays revealed enhancement of the bioactivity of SBCM-H upon complexation. Both Cu(II) and Re(I) complexes are found to be active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. TOC diagram.

Synthesis, characterisation and biological activities of S-2- or S-4-methylbenzyl-β-N-(di-2-pyridyl)methylenedithiocarbazate and Cu(II), Ni(II), Zn(II) and Cd(II) complexes

“…The π-delocalisation of charge and the configurational flexibility of their molecular chain give rise to a great variety of coordination modes [14][15][16][17][18]. Their chemistry and pharmacological applications have been widely investigated as well [1][2][3][4][5][6][15][16][17][18].Coordination compounds, especially those that contain nitrogen-sulphur ligands are synthesized via relatively simple, cost-effective procedures and it has been observed that small changes in their structure, such as change of substituents and their chelation to different metal ions cause great changes in their bioactivities. The coordination of these compounds often lead to enhanced biological activity in several pathogenic fungi [3,[19][20][21].…”

“…The coordination of these compounds often lead to enhanced biological activity in several pathogenic fungi [3,[19][20][21]. Some of these metal complexes have been known to accelerate drug action and the efficacy of a therapeutic agent [1][2][3][4][5][6][19][20][21].The Schiff bases synthesized in this study are the di-2-pyridylketone Schiff bases of isomeric dithiocarbazates, S-2-methylbenzyldithiocarbazate, S-3-methylbenzyl dithiocarbazate and S-4-methylbenzyldithiocarbazate (Fig. 1).…”

New insight into the structural, electrochemical and biological aspects of macroacyclic Cu(II) complexes derived from S-substituted dithiocarbazate schiff bases

“…4b. The seven-membered ring in CuSBHD has a half-chair conformation with the C4 atom lying 0.9970 (19)…”

“…In many cases, the biological properties of dithiocarbazate derivatives have been shown to be widely different although there may be only slight variation in their molecular structures [8]. Since these ligands possess both hard nitrogen and soft sulfur donor atoms they are capable of coordinating with a wide range of transition and non-transition metal ions forming metal complexes with interesting physicochemical and enhanced biological properties [17][18][19]. The wide diversity of structures displayed by macrocyclic and macroacyclic Schiff bases [20] result in various coordination abilities and lead to potential applications in biology ranging from therapeutics to diagnostics [21].…”

Synthesis, Characterization, Crystal Structure and Molecular Docking Studies of a S-methyldithiocarbazate Derivative: Bis[2-hydroxy- benzylidenehydrazono) (methylthio)methyl]disulfide

“…In biological systems, dithiocarbazates are extensively used as inhibitors of enzymes and for the treatment of cancer. 19,20 In early studies, Bernhardt and co-workers synthesized a series of dithiocarbazate based ligands and their iron(II) complexes and studied their antiproliferative activities. [21][22][23] Recently, Crouse et al reported copper(II) complexes of a series of Sohtun et al: Synthesis, Characterization, Crystal Structure ... dithiocarbazate Schiff base and correlated their structures and their antibacterial activity.…”